Keewaydin Island vacation rentals

We found 10,435 vacation rentals — enter your dates for availability

Welcome to the enchanting Keewaydin Island, where pristine beaches meet crystal-clear waters, inviting you to unwind in a sun-soaked paradise. Stroll through charming streets that echo local culture, and indulge in family-friendly activities that cater to all ages. Choose from cozy condos and private homes, each designed for comfort and convenience, ensuring your group enjoys the perfect blend of relaxation and adventure. Embrace the home-like experience of a vacation rental, offering the space and amenities you need for a memorable getaway.

Holiday rentals with weekly discounts - Keewaydin Island

Showing deals for:Nov 6 - Nov 13

Interior
Private kitchen
Room
Terrace/patio
Wonderful
(25 reviews)

Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!

Naples

8% off
$197
$1,381 for 7 nights
All fees included
Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!
Exterior to Home; 2 Car Garage; Courtyard Home with Privacy Fence; Walk to Vanderbilt Beach; Minutes from Mercato!
New Kitchen with All Essential Amenities; Perfect for Home Cooked Meals!
Private Pool and Hot Tub (Pool Heat Optional Add On at Time of Booking); Ample Seating; Private Grill; Privacy Fence; Southern Exposure!
Dining Table and Seating; Perfect for Home Cooked Meals!
Excellent
(10 reviews)

Sorrento 6BR Home & Private Cabana | Pool & HotTub

Naples

7% off
$683
$4,784 for 7 nights
All fees included
Sorrento 6BR Home & Private Cabana | Pool & HotTub
Interior
Pool
Private kitchen
Exterior
Exceptional
(17 reviews)

Beautiful Home with Guest House and Saltwater Pool-4 miles to beach

Naples

8% off
$673
$4,714 for 7 nights
All fees included
Beautiful Home with Guest House and Saltwater Pool-4 miles to beach
Pool
Living area
Private kitchen
Room
Exceptional
(15 reviews)

1 Min to Barefoot Beach - Heated Pool - Fully Fenced Lot

Bonita Springs

8% off
$311
$2,176 for 7 nights
All fees included
1 Min to Barefoot Beach - Heated Pool - Fully Fenced Lot
Dining
Short walk to beach, Lani Kai and shops
Private kitchen
2 raised patios with great views
Exceptional
(13 reviews)

Spacious New 6-bedroom house with Heated Pool/Spa, Elevator and WIFI

Fort Myers Beach

8% off
$977
$6,841 for 7 nights
All fees included
Spacious New 6-bedroom house with Heated Pool/Spa, Elevator and WIFI
Private kitchen
Living area
Exterior
Terrace/patio
Wonderful
(17 reviews)

🐾 Dog Friendly, Spacious Beach Retreat, only Steps to Sugary Sand, Conveniences and all the Fun!

Fort Myers Beach

7% off
$163
$1,141 for 7 nights
All fees included
🐾 Dog Friendly, Spacious Beach Retreat, only Steps to Sugary Sand, Conveniences and all the Fun!
Room
Terrace/patio
Private kitchen
Pool
Exceptional
(50 reviews)

Edgy Modern house with Heated Salt Water Pool

Naples

8% off
$299
$2,090 for 7 nights
All fees included
Edgy Modern house with Heated Salt Water Pool
Exterior
Living area
Living area
Dining
Wonderful
(21 reviews)

New to Market! 🐾 Dog Friendly, Spacious Beach Retreat, Steps to Sugary Sand, Conveniences!

Fort Myers Beach

7% off
$353
$2,473 for 7 nights
All fees included
New to Market! 🐾 Dog Friendly, Spacious Beach Retreat, Steps to Sugary Sand, Conveniences!
Terrace/patio
Pool
Private kitchen
Interior
Exceptional
(23 reviews)

Casa Bonita by the Sea. Unique upscale experience for the discerning vacationer

Bonita Springs

8% off
$540
$3,778 for 7 nights
All fees included
Casa Bonita by the Sea. Unique upscale experience for the discerning vacationer
Exterior detail
Pool
Terrace/patio
Private kitchen
Exceptional
(100 reviews)

4BR 3BA - King Suite - Heated Pool&Spa - Walk or bike to Vanderbilt Beach

Naples

8% off
$411
$2,877 for 7 nights
All fees included
4BR 3BA - King Suite - Heated Pool&Spa - Walk or bike to Vanderbilt Beach
Living Room with kitchenette
Pool
Cocktail room with access to pool and outdoors.
Fireside pool!
Exceptional
(27 reviews)

Marco Island Waterfront Single-Story Home w/ Direct Gulf Access

Marco Island

8% off
$722
$5,055 for 7 nights
All fees included
Marco Island Waterfront Single-Story Home w/ Direct Gulf Access
Pool
Living area
Private kitchen
Exterior
Exceptional
(19 reviews)

Oceanview 3-bdrm home steps from beach! Heated pool & hot tub. Sleeps 6.

Fort Myers Beach

8% off
$378
$2,647 for 7 nights
All fees included
Oceanview 3-bdrm home steps from beach! Heated pool & hot tub. Sleeps 6.
Interior
Exterior
Beach
Living area
Exceptional
(37 reviews)

Charming Home, Private Pool, Short Walk to Restaurants and Beach!

Fort Myers Beach

8% off
$376
$2,633 for 7 nights
All fees included
Charming Home, Private Pool, Short Walk to Restaurants and Beach!
Entrance door
Naples Beach!!! Just a short walk from our condo.
Interior
Outdoor dining
Exceptional
(149 reviews)

BEACH DREAMING Luxury condo, newly renovated on 5th Ave; Steps to beach & dining

Naples

17% off
$391
$2,740 for 7 nights
All fees included
BEACH DREAMING Luxury condo, newly renovated on 5th Ave; Steps to beach & dining
Private kitchen
Exterior
Living area
Pool
Exceptional
(14 reviews)

LOCATION! LOCATION! Charming 2-bedroom house in delightful Fort Myers Beach

Fort Myers Beach

8% off
$268
$1,878 for 7 nights
All fees included
LOCATION! LOCATION! Charming 2-bedroom house in delightful Fort Myers Beach
Property grounds
What a View!  From the Waterfall to the Chickee
Fitness facility
Nice morning sun! Additional seating for guests
Exceptional
(46 reviews)

'Tropical Penthouse Paradise' 5 Beaches! 2 Resort Pools! Gym! Fun!

Bonita Springs

7% off
$210
$1,468 for 7 nights
All fees included
'Tropical Penthouse Paradise' 5 Beaches! 2 Resort Pools! Gym! Fun!
Pool
Property grounds
Room
Interior
Exceptional
(61 reviews)

Estero Beach & Tennis Club, 404C, Pet Friendly- Beach Front- Internet

Fort Myers Beach

8% off
$228
$1,598 for 7 nights
All fees included
Estero Beach & Tennis Club, 404C, Pet Friendly- Beach Front- Internet
Property grounds
Beach
Interior
Interior
Exceptional
(64 reviews)

Modern Beach House...<br>Bike to beach, shopping and restaurants.

Naples

8% off
$647
$4,532 for 7 nights
All fees included
Modern Beach House...<br>Bike to beach, shopping and restaurants.
Interior
full functioning kitchen, everything you need for cooking and serving
Outdoor dining
Pool
Exceptional
(327 reviews)

Perfect recipe for relaxing, heated pool, walk to beach, bikes, stunning sunsets

Naples

8% off
$265
$1,858 for 7 nights
All fees included
Perfect recipe for relaxing, heated pool, walk to beach, bikes, stunning sunsets
Living area
Pool
Private kitchen
Private kitchen
Exceptional
(116 reviews)

The Sonset Updates Throughout Private pool near Vanderbilt Beach &Delnor Wiggins

Naples

8% off
$246
$1,722 for 7 nights
All fees included
The Sonset Updates Throughout Private pool near Vanderbilt Beach &Delnor Wiggins
Living area
Private kitchen
Pool
Lobby
Wonderful
(17 reviews)

C-224 - End Unit with Private Views & Sleeps 6

Naples

8% off
$241
$1,688 for 7 nights
All fees included
C-224 - End Unit with Private Views & Sleeps 6
Kitchen
Open floor plan. Living, Dining, and Kitchen
Dining
Lanai
Exceptional
(34 reviews)

4-bedroom vacation home just 10 minutes from 5th Ave. and beach.

Naples

8% off
$286
$2,004 for 7 nights
All fees included
4-bedroom vacation home just 10 minutes from 5th Ave. and beach.
Pool
Sport court
Gulf View form living room
Cozy Kitchen
Exceptional
(22 reviews)

Veteran Owned Beachfront, Sleeps 4.

Fort Myers Beach

8% off
$188
$1,313 for 7 nights
All fees included
Veteran Owned Beachfront, Sleeps 4.
Room
Living area
Interior
Private kitchen
Exceptional
(8 reviews)

1 Mile to the beach! Clean 2 Bedroom Cozy Duplex!

Bonita Springs

7% off
$153
$1,068 for 7 nights
All fees included
1 Mile to the beach! Clean 2 Bedroom Cozy Duplex!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Keewaydin Island

Why visit Keewaydin Island

  • Stunning Beaches: Enjoy the pristine sandy shores, perfect for sunbathing and beach activities.
  • Outdoor Adventures: Engage in fun activities like boat rentals and excursions to explore the beautiful waters.
  • Family-Friendly Atmosphere: The island caters to families, providing various options for outdoor fun and relaxation.
  • Charming Local Community: Experience the friendly vibe of nearby Naples, enhancing your vacation experience.
  • Diverse Accommodations: Choose from waterfront properties to cozy retreats, ensuring a memorable stay.

Popular types of accommodation around Keewaydin Island

Your adventure to Keewaydin Island awaits, and selecting the perfect place to stay is the first step. Explore an array of popular vacation rentals, including condos, private homes, and convenient apartments. Whether you're after waterfront properties or a cozy retreat with amenities galore, you'll find the ideal accommodation to make your getaway unforgettable. Dive into the options and secure your dream rental today.

  • Condos: The top choice for visitors to Keewaydin Island, offering modern amenities and stunning views, perfect for a relaxing getaway.
  • Houses: A great option for families and groups, these homes provide spacious living and a home-like atmosphere.
  • Apartments: A convenient choice for solo travelers or couples, featuring essential comforts in a compact space.
  • Villas: Luxurious and spacious, these properties provide a high-end vacation experience with beautiful surroundings.
  • Cottages: Quaint and cozy, ideal for a peaceful retreat near the beach or in nature.**

Top attractions near Keewaydin Island

Keewaydin Island is an ideal destination for beach lovers and families seeking outdoor adventures. Visitors can explore beautiful beaches, vibrant streets, and marinas, with activities catering to those looking for cultural experiences. Popular attractions include boat rentals and trips to Keewaydin Island, ensuring a memorable vacation filled with fun and relaxation in this picturesque setting.

  • Naples Beach: Experience the soft, white sands and stunning sunsets at Naples Beach, just 4 miles from Keewaydin Island. Enjoy beach vibes with opportunities for sunbathing, swimming, and building sandcastles, making it a perfect spot for relaxation and family fun.
  • Fifth Avenue South: A vibrant street located 5 miles away, Fifth Avenue South offers city vibes with upscale shops, art galleries, and gourmet restaurants. Stroll through this bustling area to soak in the local culture and enjoy a delightful dining experience.
  • Naples Pier: Just 4 miles from Keewaydin Island, Naples Pier features excursion vibes with fishing, dolphin watching, and scenic walks over the water. This iconic destination is perfect for enjoying beautiful ocean views and capturing memorable photographs.

Things to do recommended for couples

Looking for a romantic getaway on Keewaydin Island? Enjoy a fun round of mini-golf at Coral Cay Adventure Golf, only 5 miles away, or indulge in thrilling water sports at Marco Island Ski & Watersports, located 10 miles from the island. Perfect for couples seeking adventure.

Things to do recommended for families

Your family will have a great time at East Naples Community Park, only 3 miles away, enjoying wellness activities. For some adventure, head to Sun N Fun Lagoon, 14 miles from Keewaydin Island, a lively waterpark perfect for all ages. Eagle Lakes Community Park, 4 miles away, offers more relaxation.

Things to do recommended for groups

Groups visiting Keewaydin Island can enjoy shopping at Tin City, just 5 miles away, and experience its lively atmosphere. For outdoor enthusiasts, TPC Treviso Bay and Evergreen Golf and Country Club, both 3 to 5 miles away, offer excellent golfing opportunities in a beautiful setting.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Keewaydin Island

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Keewaydin Island with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Keewaydin Island with young kids: Traveling with little ones can be quite a challenge. It's important to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Keewaydin Island: For many families, a vacation wouldn’t feel complete without their furry companion. If this resonates with you, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Keewaydin Island: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay near Keewaydin Island

Keewaydin Island, Florida, offers a perfect blend of sandy beaches and outdoor adventures for families and couples alike. Explore the tranquil barrier island atmosphere, indulge in romantic strolls along the shore, or enjoy excursions with friendly locals. Nearby Naples enhances your experience with its vibrant community and family-friendly vibe. Whether you're seeking relaxation or adventure, Keewaydin Island is an ideal destination for your next getaway.

  • Naples: Nestled along the Gulf of Mexico, Naples is a vibrant city known for its beautiful beaches and upscale atmosphere. Keewaydin Island, located within its jurisdiction, is a serene getaway that complements the city's lively coastal charm. Visitors flock to Naples for its luxurious resorts, stunning shopping centers, and world-class golf courses. The pristine sandy beaches and family-friendly coastal parks provide a perfect backdrop for outdoor activities. Must-visit attractions include the picturesque Naples Pier and the local theme parks, which cater to both adventure seekers and families looking for fun.
  • West Naples: Just three miles from Keewaydin Island, West Naples is a charming neighborhood that offers a delightful blend of leisure and recreation. Known for its welcoming atmosphere, visitors can indulge in a variety of outdoor activities and enjoy the local beaches, perfect for families looking to unwind. The area boasts excellent shopping options, from local boutiques to larger mall centers. Golf enthusiasts will also find plenty of options to tee off. Highlights include family-friendly beaches and nearby islands that provide further opportunities for exploration and relaxation.
  • Port Royal: Port Royal is another picturesque neighborhood located approximately three miles from Keewaydin Island. This upscale enclave is famed for its stunning waterfront properties and serene environment, ideal for families and outdoor enthusiasts. Visitors can enjoy local shopping areas and top-notch golf courses while soaking in the area's natural beauty. The nearby beaches and islands make it a perfect spot for sun and sand lovers. Port Royal's exclusive atmosphere, combined with its proximity to Naples and outdoor adventures, makes it a must-visit destination during your stay.

Best time to go to Keewaydin Island

If you're planning a trip to Keewaydin Island, Naples, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March to April and June, while off-peak times, like August and October to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January65.7°F (18.7°C)No Rain (Dry)Mostly SunnyAverageAverage
February68.2°F (20.1°C)No Rain (Dry)SunnyAverageSlightly High
March70.3°F (21.3°C)No Rain (Dry)SunnySlightly HighSlightly High
April75.4°F (24.1°C)No Rain (Dry)SunnySlightly HighAverage
May78.8°F (26.0°C)Light RainMostly SunnyAverageAverage
June82.2°F (27.9°C)Light RainMostly SunnySlightly HighAverage
July83.7°F (28.7°C)Light RainMostly SunnyAverageAverage
August84.0°F (28.9°C)Light RainMostly SunnySlightly LowSlightly Low
September82.4°F (28.0°C)Light RainMostly SunnyAverageSlightly Low
October78.6°F (25.9°C)Light RainMostly SunnySlightly LowSlightly Low
November73.0°F (22.8°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December69.3°F (20.7°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway at a great value.

Vrbo Trips: Effortless planning

Vrbo's user-friendly Trip Board offers you a convenient way to plan your travel. You can start new trips, pick up right where you left off, or easily view and organize your travel plans. All the properties you’ve saved or booked are neatly categorized into Potential, Upcoming, or Current Trips for your convenience. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Travel to charming Keewaydin Island

The beaches and surrounding scenery provide a peaceful ambiance to your vacation home in Keewaydin Island. This romantic city allures visitors with its restaurants and shopping. Naples Beach and Fifth Avenue South are just a couple of the must-sees in the area. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Keewaydin Island

Do you want to find attractions to visit in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Keewaydin Island a fun place to get away. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • TPC Treviso Bay (3.2 mi / 5.1 km)
  • Flamingo Island Course - Lely Resort (5.1 mi / 8.2 km)
  • Naples Zoo at Caribbean Gardens (6.8 mi / 11 km)
  • Tiburon Golf Club (12.3 mi / 19.7 km)
  • Sun N Fun Lagoon (13.6 mi / 21.8 km)
  • La Playa Golf Club (14.5 mi / 23.4 km)

Exploring the natural features in Keewaydin Island

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Keewaydin Island is a great spot to appreciate mother nature. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Naples Beach (4.4 mi / 7.1 km)
  • Vanderbilt Beach (12.9 mi / 20.7 km)
  • Naples Botanical Garden (2.7 mi / 4.3 km)
  • East Naples Community Park (2.8 mi / 4.5 km)
  • Naples Bay (4 mi / 6.4 km)
  • Lowdermilk Beach Park (6.6 mi / 10.6 km)

Frequently asked questions

How much does it cost to rent a vacation rental in Keewaydin Island?
Property type, season and length of stay are some of the things that can determine the price of a vacation home. Simply click on your travel dates to find your perfect fit. From cozy country cottages to plush villas, all Vrbo vacation rentals offer incredible value.
How much does it cost to rent a beach house in Keewaydin Island?
When you travel and the size and style of the property will influence the cost of your beachside escape. Put in your Keewaydin Island travel dates to see your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to select the amenities and features you want in your beach house.
How old do you have to be to rent a vacation rental in Keewaydin Island?
The minimum required age is normally 16, 18 or 21. It can differ from one property to another on Vrbo, so check the rules of your preferred Keewaydin Island vacation rental before you book.
How long can I rent a vacation rental in Keewaydin Island for?
How long you can book a vacation rental in Keewaydin Island is up to the property. Just enter your preferred dates to display a list of options offering extended stays. With many features such as air conditioning and kitchens, as well as some offering discounted weekly or monthly prices, you're sure to get somewhere perfect to call your home away from home in Keewaydin Island.
Does Vrbo offer discounts for vacation homes in Keewaydin Island?
On Vrbo, we've got plenty of fabulous bargains and discounts for Keewaydin Island. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're looking for a weekend retreat or a longer stay, Vrbo has lots of options for all styles and budgets.

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